My Most Humiliating Experience Ever

When I was in my late twenties, I was in Los Angeles visiting from Long Island, NY in the mid- 1970s. LA was where you could go right off the street to a walk in S&M parlor and that’s what I did. These were the first S&M sessions that I had ever had.

The first day I picked a submissive, Slave Sheila, and had a great session with her. We got along great; she was a fine slender pretty blond submissive, a few years younger than I was. We talked and became very friendly (but that’s another story). It was so good that the next day I wanted to try a mistress. So I parked my girlfriend (she didn’t know where I was going) with friends for lunch and went to a “business” appointment.

Walking into the parlor all seemed fine. It was early in the day and I was the only customer. The manager was there - a young man my age - and we talked about neighborhoods in Long Island where, coincidentally, he was also from. There was only one mistress “on duty” at the time (Mistress Eileen) but she seemed very nice. I wrote out my fantasy (doctor’s exam, prison strip search, spanking) and she took me into the dungeon and told me to get undressed while she got ready. She also gave me a “safe” sentence for pain (“Mistress, I am a wimp and this is too much pain.”) and a safe sentence for ending the session (“Mistress, I must end the session.”

I stripped. Sitting on a cold examining table and waiting for her, I became slightly nervous, as this was my first submissive session. I covered my privates with my hand and sat there shivering.

“Hey, arms at your sides!” she barked as the entered the room. I obeyed. “Come with me.” The next thing I knew I was grabbed by my ear and led to a rack where she tied me face up.

“Well, you’re a little wimpy thing aren’t you.” She said as she walked around me brandishing a riding crop. The rack had open parts on the bottom giving her free access to my whole body. At this point I was pretty nervous since she seemed rougher and more strident than I had expected. Additionally, nothing I had written in my fantasy sheet was happening. She tapped her crop all over the parts of my body, paying particular attention to my stomach, legs and reaching under the table to slap my buttocks. The slaps were light and I began to get an erection.

“We’ll take care of that,” she said, grabbing my cock and balls. What did she mean? “I have a little surprise for you.” With that she went

As I lay there shackled to the table, Mistress Eileen said, “Wait a minute. I’ll be right back.” The air caressed my body and made me shiver but it was only a minute until she walked back in and announced, “I have a surprise for you.” In came Slave Sheila, my submissive from the day before.

I was astounded, humiliated, embarrassed; I felt my ears turning red with shame. Here I had been masterful and dominant with Sheila and she was now witnessing my submission. My penis seemed to withdraw between my legs and I closed my eyes in shame. “Hi!” Sheila blurted out, “Look what we have here!”

The two girls proceeded to walk up and down around my body lightly slapping it with riding crops. I couldn’t believe the way the session was turning out and decided to just grit my teeth and get through it.

Unlocking my hands and feet, Mistress Eileen said, “Get off the table and come over here.” I got down from the table and looked towards the Mistress and Sheila - they were in front of a pillory. “God, what’s next?” I thought to myself. I walked over to it and they placed my hands and head in and locked it up. I looked to the side and saw my hands sticking through. Further on I saw a mirror on the wall where I could see my head (I couldn’t bear to look myself in the face!) and my rear stuck out behind. What an ignominious position!

There was suddenly a knock on the door and Mistress Eileen went out of the room. Slave Sheila came over and said to me, “So how’s your vacation in LA going?” Here I was locked in a pillory, naked, expected to make small talk. I said, “Fine.” Then I heard the door opening and I heard Sheila having a conversation. She came in front of me and said, “Mistress Eileen has to pick up her son at school - he just threw up. Here is Mistress Susan! She’s our toughest Mistress.”

This tall and beautiful brunette walked in front of me and said, “Hello Allan, ready?” And then walked out of sight.

My behind exploded in pain. I looked in the mirror. Mistress Susan was holding a big leather paddle and whacking my ass good and hard (or so it seemed to be). First the right cheek, then the left, it crashed down on my buttocks. Smack! Smack! Smack! Down it came, 10 times on each cheek. I was determined to “take it like a man” and not make a sound. She said, “This is what you deserve. You’re a bad boy.”

Whack!

Whack!

Whack!

The paddle came down again. Again I looked in the mirror and saw my backside getting pinker and pinker. After about 40 whacks, she stopped. “So, how are you doing?” Slave Sheila asked me. I didn’t say anything. Without warning a crashing blow came down over both my ass cheeks simultaneously. I involuntarily said, “OUCH!” “That got you talking!” Mistress Susan commented.

With that she continued the onslaught. Each time the paddle came down I let out either an involuntary grunt of pain or said “OUCH!” I looked in the mirror and saw Slave Sheila smiling at me. I also saw my buttocks were getting red and I was starting to sweat.

Whack! Grunt.

Whack!

Harder whack! “Ouch!”

Even harder. “OWW!”

“I can’t be marked for long. My girlfriend will see!” I said.

“I can’t be marked for long, MISTRESS!” She corrected me and brought the paddle down sharply on my left thigh. It stung like the dickens but I remained mute. She brought it down on my right thigh. It was even worse. Finally, I capitulated, “I can’t be marked for long, Mistress!” I looked in the mirror and my hands were kind of “clawing” the air. I was panting and sweating and shaking my burning legs. Sheila and Mistress Susan were smiling.

Mistress said, “That was the last one. We’ll go on to something different now.” She bent down and looked me in the eye at “pillory level,” saying, “You’ve been pretty dull up to now, Allen. And it doesn’t seem like you can take much pain. So you’re embarrassment is going to amuse us next.” Mistress again disappeared from view. The next thing I knew I felt a tape on my left behind cheek. I looked in the mirror and saw, to my utter horror and mortification, a leather “tail” taped securely to my butt.

“Dance, pony boy.” Said Mistress Susan. Turning puce with shame I moved my feet in an up and down motion. “Dance better or I’ll hit you with this!” “This” was the biggest wooden paddle I had ever seen - with holes drilled into it. Boy, did I dance! I moved my ass this way and that. Mistress said right, I moved my behind to the right. Left and I moved to the left. I was deathly afraid of that big paddle - the pain and marks for my girlfriend to see.

“OK, that’s funny enough,” the Mistress said. “Onto our next activity. Sheila, go over to watch Allen’s face.” Sheila appeared again in front of me. This time Mistress Susan whispered in my ear. “I bet I can make you flinch. On the count of three I’m going to rip off the tape holding that tail to your ass. One, two, three!”

I held my breath, waiting for the pain. None came. “Sheila, is his face as scrunched up as his ass?”

“It sure is!” Sheila and Mistress Susan both broke out laughing. I looked in the mirror to the side. My buttocks were all clenched together protecting themselves from the potential pain of the tape removal. But the tail was still humiliating me by hanging there.

By this time I was wondering when the session would end and I would get out of this place. I was breathing long deep breaths to try to steady myself. Without warning I heard myself suddenly say, “Ahhh - OUCH!” And I felt a stinging pain in the butt - Mistress had ripped off the tape without warning. There was a red splotch on the left cheek of my red and pink buttocks.

“Little boy, do you remember your safe word?” Mistress Susan asked. I nodded my head (as much as you can in a pillory), scared to death now. Why would she ask me that? “Here it comes.” She gleefully said.

“OWWWWWWWW!” I screamed. Later I saw that Mistress Susan had taken a gigantic spring loaded paper clip type device and attached it to my left butt cheek, just where buttock meets thigh. “Mistress, I am a wimp and this is too much pain!” I shrieked as loud as I could. The two mistresses, for now that was how I saw them - Sheila was hardly my slave any more, were treated to the sight of a young man gyrating wildly. In the process, thank God, the clothespin came off my poor behind.

At least the Mistress was honorable in this regard and I saw her come over and lift up the top of the pillory, releasing my head and hands. I sank down to the floor, on my side, soothing and rubbing my left cheek and thigh. That side seemed to be the mistresses’ favorite - it had absorbed most of the damage. I prayed that the session was over but a small shred of pride wouldn’t let me use that last safe word.

Mistress Susan towered over me, “Get up! One more thing to go!”

“Oh my God!” I thought to myself, “I forgot the enema.” How could I stand any more? I was beaten and humiliated, sweat pouring off my body, rubbing my behind like a little child. Former Slave Sheila picked me up by my ear as we marched toward the enema room. Mistress Susan followed behind. I didn’t trust her, so I was forced to practically waddle behind Sheila with my hands behind me, palms facing outward, guarding my vulnerable punished behind. I presented some sight!

Into the medical room we went and the mistresses (Sheila could hardly be called a slave any more) made me get onto the examination table and lie on my stomach. By this time my buttocks had a life of their own and they clenched together protectively as tight as two snare drums. Mistress Susan stuck her finger at the bottom of my bottom, right at my most vulnerable part. I could feel the lubricant on it (no exam gloves - remember, this was years before AIDS).

“Loosen up, little boy, or I’ll hurt you.” She commanded.

“I’m trying.” I whimpered back, now reduced to a whiny pre-pubescent state.

“Oh forget it!” She said, disgustedly. “You’re really a pretty dull slave, boy. I must say.” With that I felt her finger press firmly at the “heart of the matter,” right into my anus, past the sphincter ring, into my rectum. I squeaked and squirmed under her invasion. Never before or since have I felt humiliation like this. It was washing over me in waves and I was almost crying. She withdrew her finger and I breathed again. I heard Sheila laughing in the background, “Oh he looks so cute,” she commented.

Next came the invasion of the tube. Once again my bottom was locked to invaders but her lubrication had done its trick - the hose went in and in. And in and in some more. This was only the second enema of my life but I knew the tubing was snaking in too far. “Oh no!” I thought, “She’s giving me a high colonic!” And then the soapy water started to enter. If you can believe I forgot the demeaning tube hanging out of my anus I did - all I could think of was the water rushing into my stomach and the cramping.

Mistress leaned down and whispered in my ear, “If anything comes out of your cock or your asshole I’m making you lick it up!”

“Please, that’s enough, let me go to the bathroom.” I pleaded. But Mistress Susan was relentless. I probably took only about 2 quarts or so, but I felt stuffed with a gallon. Finally, I felt the embarrassing journey of the tube out of my anus begin. It slithered and slithered and as it passed my anal ring I had at first a sense of relief that the session was finally over and then an impending worry about my need to evacuate my bowels.

I was worried but Mistress Susan probably didn’t want her “office” messed up any more than I wanted to lose control. So she quickly pressed a big wad of toilet paper into my bottom crack, took my hand and said, “Press hard boy!”

And boy, did I press hard! She gave me a towel and said. “You have to go through the hallway to the bathroom. There may be some other customers there. Put this towel around you. And don’t forget to hold that toilet paper there.” With that she helped me off the table. It was easier said than done. With one hand in back of me I pushed a wad of toilet paper literally into my ass; with the other I held a towel covering my cock. In this ridiculous manner I got off the table.

Both mistresses stopped at the door, “You were a dull slave, but I hope you had a good time. Your clothes are in the locker room. Goodbye.” Again I waddled. This time out to the bathroom, trying to sneak in without anyone seeing - one hand in front, one in back (literally IN back!). I didn’t meet any customers but I did see the parlor manager on the way to the bathroom. He smiled and winked at me and said, “Hope you had a good time! See you around Long Island some day!”

Completely ashamed and humiliated I emptied my bowels in the bathroom as quickly as possible and left the parlor.

One final embarrassing note. In the car driving back to my hotel, I realized there was still some water left in me, soapy to judge by the burning sensation. I’m sure other drivers noticed me squirming as we stopped at red lights. I had to stop at the nearest gas station and run to the men’s room. Shock of all shocks, it was there that my horror turned to arousal. I masturbated to climax in about 2 minutes.

That experience was certainly awful, but it has made me horny many times over the past 20 years. But it remains my most humiliating experience ever.

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